In some cases, new window units fit
inside old jambs.  However, if the old
window is a double hung unit with
counterweights, replace the entire
unit -- hollow sash weight channels
allow significant heat loss.

Determine the dimensions for the new
window by removing only the inside
casings and stool and measuring the
distance from side to side between
the studs and from top to bottom
between the header and rough sill. 
Since the opening may not be square,
take several measurements.  Order the
largest window that will fit in the
opening, or have a window custom
built to fit.  You may also want to
enlarge and reframe the opening for a
larger window.

If the window is small, 2 feet by 3 feet for instance, remove it as one unit.  If it is larger, take out the sash before removing jambs and sill.

1.
Start from the inside.  Remove the interior casings and stool so that you can measure the rough window opening and specify a new window.  When it is time to remove the existing window, cut the sash cords and remove the sash weights separately.  If the window is small, you can leave them in, if it is easier.  Remove the apron.

2.  If you plan to reuse the unit, cut all the nails that hold the jambs to the studs, then pry the casing away from the exterior wall.  The entire window will come with them.  The unit is intact and ready for reuse.  If you are not reusing the unit, pry off the exterior casing before cutting the nails.

3.  Use a hacksaw to cut the nails that hold the jambs to the trimmer studs.  These nails may be easier to reach from the inside.  Without the nails, the window should swing out when you pull on it.  Be careful if you are on a ladder.  Be sure you remove the sash weights.  You may want to even remove the sash.

Installing a window in an existing opening.  Measure the rough opening.  There should be 1/4 to 1/2-inch clearance all around.  If the opening is too large, nail spacer boards to the studs.  If there is no building paper around the opening, loosen the siding boards, and tuck flashing paper under them as far as you can.  Trim the paper flush with the opening or wrap it around the studs.  If the new window does not come with preformed flashing or drip cap, cut a piece of aluminum flashing to fit across the top of the window, and tuck it 3 or 4 inches under the siding.  Bend it outward so it covers the drip cap or the top casing of the new window.  Nail the siding boards back in place.

How To Remove A Wood Window

In A Hour.com
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